Former Pirates manager reacts to investment he didn't get to see

The Pittsburgh Pirates beat the Minnesota Twins 6-4 on Thursday, marking the team's Grapefruit League-best fifth win already this spring. But the biggest storyline from that contest came not from what happened on the field, but rather from someone in the visiting dugout.

That game marked the first of the spring between the Bucs and the Twins, who are now managed by ex-Pirates skipper Derek Shelton. Shelton, of course, managed the Pirates for five-plus seasons before being let go after the team lost 26 of its first 38 games to begin the 2025 season.

On the heels of a seventh consecutive losing season (thanks to MLB's worst offense), the Pirates had their most aggressive offseason in quite some time. They addressed that offense by adding Ryan O'Hearn and Marcell Ozuna in free agency and trading for Brandon Lowe, Jake Mangum, and Jhostynxon Garcia.

Shelton met with Pirates media before Thursday's game and, naturally, was asked about the timing of the team's uncharacteristically active winter.

"I think at some point you wish you would have seen the investment that they saw this offseason, but good for them," Shelton told reporters before Thursday's contest. He went on to express how happy he is for Pirates fans, and for Ben Cherington specifically, about the club's additions.

There wasn't anything about the tone in which Shelton made those comments that would suggest that he's harboring any resentment about his time in Pittsburgh or the way his managerial tenure ended. But it's difficult not to speculate that he might feel that way.

Ex-Pirates manager Derek Shelton responds to the team finally spending

Shelton and Cherington came to Pittsburgh around the same time and failed to produce a winner for five seasons (the Pirates' GM even claimed that the pair would enter year six "accountable together"). The 2025 season quickly went off the rails, leading to Shelton's firing in May, while Cherington was permitted to stay—not only for the remainder of the 2025 campaign, but into this season as well. And it wasn't until this offseason that Cherington received clearance to push the Pirates' payroll to levels that the franchise has never seen before.

Shelton was reportedly irked for weeks after the Pirates let him go (and also admitted to reporters that he didn't follow the team after his firing), though taking a summer off to reflect on his Pittsburgh tenure and quickly landing another managerial gig surely dampened those emotions. But it would be fair for him to be annoyed at the Pirates' sudden splurge after seeing some of the rosters he was afforded as the club's manager.

There were only really two instances where it seemed like the Pirates were "going for it" (and even that might be stretching things) while Shelton was in Pittsburgh. The first was before the 2023 season, where, after the team played at a 102-loss pace through the first three seasons of the Cherington-Shelton regime, there was an influx of veteran leadership brought aboard to stabilize an otherwise very young roster.

That offseason saw the Bucs trade for Ji-man Choi and Connor Joe while making multiple free agent additions, most notably Carlos Santana, Rich Hill, Austin Hedges, and the initial reunion with Andrew McCutchen. The Pirates roared out to a 20-8 start but plodded through a 1-10 stretch in early May and a 1-12 stretch in the middle of June that sealed the team's fate.

The other instance came the following season, when the Pirates—fueled by rookies Paul Skenes and Jared Jones atop the starting rotation—entered the trade deadline at 55-52 and within striking distance of a playoff spot. Operating as trade deadline buyers for the first time in ages, the Pirates attempted to fortify their squad with Bryan De La Cruz (who posted a .514 OPS and promptly got non-tendered) and Isiah Kiner-Falefa (who at least was able to stick around into 2025 but was waived in August after he had no takers at the trade deadline).

It has to be disheartening for Shelton to see Pittsburgh go from that to what the team added this offseason—a pair of 2025 All-Star bats, another hitter who's a three-time All-Star and two seasons removed from a top-five NL MVP finish, an MLB-ready top-100 outfield prospect, and a two-time All-Star reliever, among other pieces. It probably doesn't help that the club Shelton now manages just underwent an all-time trade deadline fire sale amid questions surrounding the future of the team's ownership and has already been dealt a brutal hit with injuries this spring.

Shelton has been around Major League Baseball for a long time. He knows how to conduct himself with class, respect, and professionalism, and his sit-down with Pirates media indicated that.

Given his frustration after being fired last season and the stark contrast in the front office's actions since he left, it's fair to wonder if Shelton feels at least a little resentful that the team waited this long to make these kinds of additions to the big-league roster. It certainly wouldn't be hard to blame him.